diff --git a/build-support/bin/generate_docs.py b/build-support/bin/generate_docs.py
index 10e301bd983..61ae5ce4660 100644
--- a/build-support/bin/generate_docs.py
+++ b/build-support/bin/generate_docs.py
@@ -33,6 +33,7 @@
 from common import die
 
 from pants.help.help_info_extracter import to_help_str
+from pants.util.docutil import DocUrlMatcher, DocUrlRewriter, get_titles
 from pants.version import MAJOR_MINOR
 
 logger = logging.getLogger(__name__)
@@ -40,10 +41,20 @@
 
 def main() -> None:
     logging.basicConfig(format="[%(levelname)s]: %(message)s", level=logging.INFO)
-    version = determine_pants_version()
     args = create_parser().parse_args()
+    version = determine_pants_version()
     help_info = run_pants_help_all()
-    generator = ReferenceGenerator(args, version, help_info)
+    doc_urls = DocUrlMatcher().find_doc_urls(value_strs_iter(help_info))
+    logger.info("Found the following docsite URLs:")
+    for url in sorted(doc_urls):
+        logger.info(f"  {url}")
+    logger.info("Fetching titles...")
+    slug_to_title = get_titles(doc_urls)
+    logger.info("Found the following titles:")
+    for slug, title in sorted(slug_to_title.items()):
+        logger.info(f"  {slug}: {title}")
+    rewritten_help_info = rewrite_value_strs(help_info, slug_to_title)
+    generator = ReferenceGenerator(args, version, rewritten_help_info)
     if args.sync:
         generator.sync()
     else:
@@ -142,8 +153,41 @@ def run_pants_help_all() -> Dict:
     return cast(Dict, json.loads(run.stdout))
 
 
+def value_strs_iter(help_info: dict) -> Iterable[str]:
+    def _recurse(val: Any) -> Iterable[str]:
+        if isinstance(val, str):
+            yield val
+        if isinstance(val, dict):
+            for v in val.values():
+                for x in _recurse(v):
+                    yield x
+        if isinstance(val, list):
+            for v in val:
+                for x in _recurse(v):
+                    yield x
+
+    for x in _recurse(help_info):
+        yield x
+
+
+def rewrite_value_strs(help_info: dict, slug_to_title: dict[str, str]) -> dict:
+    """Return a copy of the argument with rewritten docsite URLs."""
+    rewriter = DocUrlRewriter(slug_to_title)
+
+    def _recurse(val: Any) -> Any:
+        if isinstance(val, str):
+            return rewriter.rewrite(val)
+        if isinstance(val, dict):
+            return {k: _recurse(v) for k, v in val.items()}
+        if isinstance(val, list):
+            return [_recurse(x) for x in val]
+        return val
+
+    return cast(dict, _recurse(help_info))
+
+
 class ReferenceGenerator:
-    def __init__(self, args: argparse.Namespace, version: str, help_info: Dict) -> None:
+    def __init__(self, args: argparse.Namespace, version: str, help_info: dict) -> None:
         self._args = args
         self._version = version
 
@@ -177,7 +221,7 @@ def _link(scope: str, *, sync: bool) -> str:
         return f"reference-{url_safe_scope}" if sync else f"{url_safe_scope}.md"
 
     @classmethod
-    def process_options_input(cls, help_info: Dict, *, sync: bool) -> Dict:
+    def process_options_input(cls, help_info: dict, *, sync: bool) -> Dict:
         scope_to_help_info = help_info["scope_to_help_info"]
 
         # Process the list of consumed_scopes into a comma-separated list, and add it to the option
diff --git a/build-support/bin/generate_docs_test.py b/build-support/bin/generate_docs_test.py
index 44c9b0f2572..94cfe720b27 100644
--- a/build-support/bin/generate_docs_test.py
+++ b/build-support/bin/generate_docs_test.py
@@ -1,7 +1,7 @@
 # Copyright 2021 Pants project contributors (see CONTRIBUTORS.md).
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
-from generate_docs import html_safe, markdown_safe
+from generate_docs import html_safe, markdown_safe, value_strs_iter
 
 
 def test_markdown_safe():
@@ -10,3 +10,14 @@ def test_markdown_safe():
 
 def test_html_safe():
     assert "foo <code>bar==&#x27;baz&#x27;</code> qux" == html_safe("foo `bar=='baz'` qux")
+
+
+def test_gather_value_strs():
+    help_info = {
+        "a": "foo",
+        "b": ["bar", 5, "baz"],
+        "c": 42,
+        "d": True,
+        "e": {"f": 5, "g": "qux", "h": {"i": "quux"}},
+    }
+    assert set(value_strs_iter(help_info)) == {"foo", "bar", "baz", "qux", "quux"}
diff --git a/src/python/pants/backend/awslambda/python/rules.py b/src/python/pants/backend/awslambda/python/rules.py
index 9de7c479281..f3a3e5c0da9 100644
--- a/src/python/pants/backend/awslambda/python/rules.py
+++ b/src/python/pants/backend/awslambda/python/rules.py
@@ -40,7 +40,7 @@
     targets_with_sources_types,
 )
 from pants.engine.unions import UnionMembership, UnionRule
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.logging import LogLevel
 
 logger = logging.getLogger(__name__)
@@ -119,7 +119,7 @@ async def package_python_awslambda(
             "files targets, but Pants will not include them in the built Lambda. Filesystem APIs "
             "like `open()` are not able to load files within the binary itself; instead, they "
             "read from the current working directory."
-            f"\n\nInstead, use `resources` targets. See {bracketed_docs_url('resources')}."
+            f"\n\nInstead, use `resources` targets. See {doc_url('resources')}."
             f"\n\nFiles targets dependencies: {files_addresses}"
         )
 
diff --git a/src/python/pants/backend/awslambda/python/target_types.py b/src/python/pants/backend/awslambda/python/target_types.py
index 833a40662e3..1cf3d6910ec 100644
--- a/src/python/pants/backend/awslambda/python/target_types.py
+++ b/src/python/pants/backend/awslambda/python/target_types.py
@@ -30,7 +30,7 @@
 from pants.engine.unions import UnionRule
 from pants.source.filespec import Filespec
 from pants.source.source_root import SourceRoot, SourceRootRequest
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 
 
 class DeprecatedAwsLambdaInterpreterConstraints(InterpreterConstraintsField):
@@ -205,8 +205,8 @@ class PythonAWSLambda(Target):
         PythonAwsLambdaRuntime,
     )
     help = (
-        "A self-contained Python function suitable for uploading to AWS Lambda.\n\nSee "
-        f"{bracketed_docs_url('awslambda-python')}."
+        "A self-contained Python function suitable for uploading to AWS Lambda.\n\n"
+        f"See {doc_url('awslambda-python')}."
     )
 
 
diff --git a/src/python/pants/backend/codegen/protobuf/python/python_protobuf_subsystem.py b/src/python/pants/backend/codegen/protobuf/python/python_protobuf_subsystem.py
index 1e1754f455d..6ea1debeb14 100644
--- a/src/python/pants/backend/codegen/protobuf/python/python_protobuf_subsystem.py
+++ b/src/python/pants/backend/codegen/protobuf/python/python_protobuf_subsystem.py
@@ -11,14 +11,12 @@
 from pants.engine.unions import UnionRule
 from pants.option.custom_types import target_option
 from pants.option.subsystem import Subsystem
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 
 
 class PythonProtobufSubsystem(Subsystem):
     options_scope = "python-protobuf"
-    help = (
-        f"Options related to the Protobuf Python backend.\n\nSee {bracketed_docs_url('protobuf')}."
-    )
+    help = f"Options related to the Protobuf Python backend.\n\nSee {doc_url('protobuf')}."
 
     @classmethod
     def register_options(cls, register):
diff --git a/src/python/pants/backend/codegen/protobuf/target_types.py b/src/python/pants/backend/codegen/protobuf/target_types.py
index 8b4f47b3b1a..e3d5edaf5f9 100644
--- a/src/python/pants/backend/codegen/protobuf/target_types.py
+++ b/src/python/pants/backend/codegen/protobuf/target_types.py
@@ -2,11 +2,12 @@
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
 from pants.engine.target import COMMON_TARGET_FIELDS, BoolField, Dependencies, Sources, Target
-from pants.util.docutil import bracketed_docs_url
-
 
 # NB: We subclass Dependencies so that specific backends can add dependency injection rules to
 # Protobuf targets.
+from pants.util.docutil import doc_url
+
+
 class ProtobufDependencies(Dependencies):
     pass
 
@@ -25,4 +26,4 @@ class ProtobufGrpcToggle(BoolField):
 class ProtobufLibrary(Target):
     alias = "protobuf_library"
     core_fields = (*COMMON_TARGET_FIELDS, ProtobufDependencies, ProtobufSources, ProtobufGrpcToggle)
-    help = f"Protobuf files used to generate various languages.\n\nSee {bracketed_docs_url('protobuf')}."
+    help = f"Protobuf files used to generate various languages.\n\nSee f{doc_url('protobuf')}."
diff --git a/src/python/pants/backend/python/goals/package_pex_binary.py b/src/python/pants/backend/python/goals/package_pex_binary.py
index be53099e0d2..231919df49b 100644
--- a/src/python/pants/backend/python/goals/package_pex_binary.py
+++ b/src/python/pants/backend/python/goals/package_pex_binary.py
@@ -44,7 +44,7 @@
     targets_with_sources_types,
 )
 from pants.engine.unions import UnionMembership, UnionRule
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.logging import LogLevel
 
 logger = logging.getLogger(__name__)
@@ -120,8 +120,8 @@ async def package_pex_binary(
             "targets, but Pants will not include them in the PEX. Filesystem APIs like `open()` "
             "are not able to load files within the binary itself; instead, they read from the "
             "current working directory."
-            "\n\nInstead, use `resources` targets or wrap this `pex_binary` in an `archive`. See "
-            f"{bracketed_docs_url('resources')}."
+            "\n\nInstead, use `resources` targets or wrap this `pex_binary` in an `archive`. "
+            f"See {doc_url('resources')}."
             f"\n\nFiles targets dependencies: {files_addresses}"
         )
 
diff --git a/src/python/pants/backend/python/goals/setup_py.py b/src/python/pants/backend/python/goals/setup_py.py
index 570e0e88961..164b517d492 100644
--- a/src/python/pants/backend/python/goals/setup_py.py
+++ b/src/python/pants/backend/python/goals/setup_py.py
@@ -61,7 +61,7 @@
 from pants.engine.unions import UnionMembership, UnionRule, union
 from pants.option.subsystem import Subsystem
 from pants.python.python_setup import PythonSetup
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.logging import LogLevel
 from pants.util.memo import memoized_property
 from pants.util.meta import frozen_after_init
@@ -88,7 +88,7 @@ class OwnershipError(Exception):
 
     def __init__(self, msg: str):
         super().__init__(
-            f"{msg} See {bracketed_docs_url('python-distributions')} for "
+            f"{msg} See {doc_url('python-distributions')} for "
             f"how python_library targets are mapped to distributions."
         )
 
diff --git a/src/python/pants/backend/python/lint/pylint/subsystem.py b/src/python/pants/backend/python/lint/pylint/subsystem.py
index 2237935624e..c2d7b1ee17d 100644
--- a/src/python/pants/backend/python/lint/pylint/subsystem.py
+++ b/src/python/pants/backend/python/lint/pylint/subsystem.py
@@ -11,7 +11,7 @@
 from pants.core.util_rules.config_files import ConfigFilesRequest
 from pants.engine.addresses import UnparsedAddressInputs
 from pants.option.custom_types import file_option, shell_str, target_option
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 
 
 class Pylint(PythonToolBase):
@@ -74,7 +74,7 @@ def register_options(cls, register):
                 "example, if your plugin is at `build-support/pylint/custom_plugin.py`, add "
                 "'build-support/pylint' to `[source].root_patterns` in `pants.toml`. This is "
                 "necessary for Pants to know how to tell Pylint to discover your plugin. See "
-                f"{bracketed_docs_url('source-roots')}\n\nYou must also set `load-plugins=$module_name` in "
+                f"{doc_url('source-roots')}\n\nYou must also set `load-plugins=$module_name` in "
                 "your Pylint config file, and set the `[pylint].config` option in `pants.toml`."
                 "\n\nWhile your plugin's code can depend on other first-party code and third-party "
                 "requirements, all first-party dependencies of the plugin must live in the same "
diff --git a/src/python/pants/backend/python/target_types.py b/src/python/pants/backend/python/target_types.py
index 0e454e49910..db03ce437ab 100644
--- a/src/python/pants/backend/python/target_types.py
+++ b/src/python/pants/backend/python/target_types.py
@@ -46,7 +46,7 @@
 from pants.option.subsystem import Subsystem
 from pants.python.python_setup import PythonSetup
 from pants.source.filespec import Filespec
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.frozendict import FrozenDict
 
 logger = logging.getLogger(__name__)
@@ -69,9 +69,9 @@ class InterpreterConstraintsField(StringSequenceField):
         "`CPython` as a shorthand, e.g. '>=2.7' will be expanded to 'CPython>=2.7'.\n\nSpecify "
         "more than one element to OR the constraints, e.g. `['PyPy==3.7.*', 'CPython==3.7.*']` "
         "means either PyPy 3.7 _or_ CPython 3.7.\n\nIf the field is not set, it will default to "
-        "the option `[python-setup].interpreter_constraints`.\n\nSee "
-        f"{bracketed_docs_url('python-interpreter-compatibility')} for how these interpreter "
-        f"constraints are merged with the constraints of dependencies."
+        "the option `[python-setup].interpreter_constraints`.\n\n"
+        f"See {doc_url('python-interpreter-compatibility')} for how these interpreter "
+        "constraints are merged with the constraints of dependencies."
     )
 
     def value_or_global_default(self, python_setup: PythonSetup) -> Tuple[str, ...]:
@@ -390,7 +390,7 @@ class PexBinary(Target):
     help = (
         "A Python target that can be converted into an executable PEX file.\n\nPEX files are "
         "self-contained executable files that contain a complete Python environment capable of "
-        f"running the target. For more information, see {bracketed_docs_url('pex-files')}."
+        f"running the target. For more information, see {doc_url('pex-files')}."
     )
 
 
@@ -471,7 +471,7 @@ class PythonTests(Target):
     help = (
         "Python tests, written in either Pytest style or unittest style.\n\nAll test util code, "
         "other than `conftest.py`, should go into a dedicated `python_library()` target and then "
-        f"be included in the `dependencies` field.\n\nSee {bracketed_docs_url('python-test-goal')}."
+        f"be included in the `dependencies` field.\n\nSee {doc_url('python-test-goal')}."
     )
 
 
@@ -650,7 +650,7 @@ class PythonRequirementLibrary(Target):
         "Python requirements inline in a BUILD file. If you have a `requirements.txt` file "
         "already, you can instead use the macro `python_requirements()` to convert each "
         "requirement into a `python_requirement_library()` target automatically.\n\nSee "
-        f"{bracketed_docs_url('python-third-party-dependencies')}."
+        f"{doc_url('python-third-party-dependencies')}."
     )
 
 
@@ -710,8 +710,8 @@ class PythonProvidesField(ScalarField, ProvidesField):
         "`name`. You can also set almost any keyword argument accepted by setup.py in the "
         "`setup()` function: "
         "(https://packaging.python.org/guides/distributing-packages-using-setuptools/#setup-args)."
-        f"\n\nSee {bracketed_docs_url('plugins-setup-py')} for how to write a plugin to "
-        f"dynamically generate kwargs."
+        f"\n\nSee {doc_url('plugins-setup-py')} for how to write a plugin to "
+        "dynamically generate kwargs."
     )
 
     @classmethod
@@ -742,5 +742,5 @@ class PythonDistribution(Target):
     )
     help = (
         "A publishable Python setuptools distribution (e.g. an sdist or wheel).\n\nSee "
-        f"{bracketed_docs_url('python-distributions')}."
+        f"{doc_url('python-distributions')}."
     )
diff --git a/src/python/pants/backend/python/typecheck/mypy/rules.py b/src/python/pants/backend/python/typecheck/mypy/rules.py
index 0bc12db39be..fd1436b3402 100644
--- a/src/python/pants/backend/python/typecheck/mypy/rules.py
+++ b/src/python/pants/backend/python/typecheck/mypy/rules.py
@@ -34,7 +34,7 @@
 from pants.engine.target import FieldSet, Target, TransitiveTargets, TransitiveTargetsRequest
 from pants.engine.unions import UnionRule
 from pants.python.python_setup import PythonSetup
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.logging import LogLevel
 from pants.util.ordered_set import FrozenOrderedSet, OrderedSet
 from pants.util.strutil import pluralize
@@ -99,7 +99,7 @@ def check_and_warn_if_python_version_configured(
         logger.warning(
             f"You set {formatted_configured}. Normally, Pants would automatically set this for you "
             "based on your code's interpreter constraints "
-            f"({bracketed_docs_url('python-interpreter-compatibility')}). Instead, it will "
+            f"({doc_url('python-interpreter-compatibility')}). Instead, it will "
             "use what you set.\n\n(Automatically setting the option allows Pants to partition your "
             "targets by their constraints, so that, for example, you can run MyPy on Python 2-only "
             "code and Python 3-only code at the same time. This feature may no longer work.)"
diff --git a/src/python/pants/core/goals/tailor.py b/src/python/pants/core/goals/tailor.py
index fd8b051c9b3..c7465128232 100644
--- a/src/python/pants/core/goals/tailor.py
+++ b/src/python/pants/core/goals/tailor.py
@@ -35,6 +35,7 @@
     UnexpandedTargets,
 )
 from pants.engine.unions import UnionMembership, union
+from pants.util.docutil import doc_url
 from pants.util.frozendict import FrozenDict
 from pants.util.logging import LogLevel
 from pants.util.memo import memoized
@@ -227,7 +228,7 @@ def register_options(cls, register):
             type=dict,
             help="A mapping from standard target type to custom type to use instead. The custom "
             "type can be a custom target type or a macro that offers compatible functionality "
-            "to the one it replaces (see https://www.pantsbuild.org/docs/macros).",
+            f"to the one it replaces (see {doc_url('macros')}).",
         )
 
     @property
diff --git a/src/python/pants/engine/internals/graph.py b/src/python/pants/engine/internals/graph.py
index efa7e6fae76..0da0f34900c 100644
--- a/src/python/pants/engine/internals/graph.py
+++ b/src/python/pants/engine/internals/graph.py
@@ -76,7 +76,7 @@
 from pants.engine.unions import UnionMembership
 from pants.option.global_options import GlobalOptions, OwnersNotFoundBehavior
 from pants.source.filespec import matches_filespec
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.logging import LogLevel
 from pants.util.ordered_set import FrozenOrderedSet, OrderedSet
 
@@ -418,9 +418,9 @@ def _log_or_raise_unmatched_owners(
             f"target whose `sources` field includes the file."
         )
     msg = (
-        f"{prefix} See {bracketed_docs_url('targets')} for more information on target definitions."
+        f"{prefix} See {doc_url('targets')} for more information on target definitions."
         f"\n\nYou may want to run `./pants tailor` to autogenerate your BUILD files. See "
-        f"{bracketed_docs_url('create-initial-build-files')}.{option_msg}"
+        f"{doc_url('create-initial-build-files')}.{option_msg}"
     )
 
     if owners_not_found_behavior == OwnersNotFoundBehavior.warn:
diff --git a/src/python/pants/engine/internals/parser.py b/src/python/pants/engine/internals/parser.py
index 9c3ce07bdb2..37bec51c8f5 100644
--- a/src/python/pants/engine/internals/parser.py
+++ b/src/python/pants/engine/internals/parser.py
@@ -12,7 +12,7 @@
 from pants.base.parse_context import ParseContext
 from pants.build_graph.build_file_aliases import BuildFileAliases
 from pants.engine.internals.target_adaptor import TargetAdaptor
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.frozendict import FrozenDict
 
 
@@ -105,7 +105,7 @@ def parse(
             original = e.args[0].capitalize()
             help_str = (
                 "If you expect to see more symbols activated in the below list,"
-                f" refer to {bracketed_docs_url('enabling-backends')} for all available"
+                f" refer to {doc_url('enabling-backends')} for all available"
                 " backends to activate."
             )
 
@@ -142,6 +142,6 @@ def error_on_imports(build_file_content: str, filepath: str) -> None:
         raise ParseError(
             f"Import used in {filepath} at line {lineno}. Import statements are banned in "
             "BUILD files because they can easily break Pants caching and lead to stale results. "
-            f"\n\nInstead, consider writing a macro ({bracketed_docs_url('macros')}) or "
-            f"writing a plugin ({bracketed_docs_url('plugins-overview')}."
+            f"\n\nInstead, consider writing a macro ({doc_url('macros')}) or "
+            f"writing a plugin ({doc_url('plugins-overview')}."
         )
diff --git a/src/python/pants/engine/internals/parser_test.py b/src/python/pants/engine/internals/parser_test.py
index be2ace3bf01..06cecbc6da9 100644
--- a/src/python/pants/engine/internals/parser_test.py
+++ b/src/python/pants/engine/internals/parser_test.py
@@ -7,7 +7,7 @@
 
 from pants.build_graph.build_file_aliases import BuildFileAliases
 from pants.engine.internals.parser import BuildFilePreludeSymbols, ParseError, Parser
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.frozendict import FrozenDict
 
 
@@ -37,7 +37,7 @@ def perform_test(extra_targets: list[str], dym: str) -> None:
         assert str(exc.value) == (
             f"Name 'fake' is not defined.\n\n{dym}"
             "If you expect to see more symbols activated in the below list,"
-            f" refer to {bracketed_docs_url('enabling-backends')} for all available"
+            f" refer to {doc_url('enabling-backends')} for all available"
             " backends to activate.\n\n"
             f"All registered symbols: ['caof', {fmt_extra_sym}'obj', 'prelude', 'tgt']"
         )
diff --git a/src/python/pants/engine/target.py b/src/python/pants/engine/target.py
index e36a00d2da8..5cb6c6d54ee 100644
--- a/src/python/pants/engine/target.py
+++ b/src/python/pants/engine/target.py
@@ -46,7 +46,7 @@
 from pants.option.global_options import FilesNotFoundBehavior
 from pants.source.filespec import Filespec, matches_filespec
 from pants.util.collections import ensure_list, ensure_str_list
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.frozendict import FrozenDict
 from pants.util.memo import memoized_classproperty, memoized_method, memoized_property
 from pants.util.meta import frozen_after_init
@@ -1663,7 +1663,7 @@ def maybe_warn_of_ambiguous_dependency_inference(
             f"with `!` or `!!` so that one or no targets are left."
             f"\n\nAlternatively, you can remove the ambiguity by deleting/changing some of the "
             f"targets so that only 1 target owns this {import_reference}. Refer to "
-            f"{bracketed_docs_url('troubleshooting#import-errors-and-missing-dependencies')}."
+            f"{doc_url('troubleshooting#import-errors-and-missing-dependencies')}."
         )
 
     def disambiguated_via_ignores(self, ambiguous_addresses: tuple[Address, ...]) -> Address | None:
diff --git a/src/python/pants/goal/anonymous_telemetry.py b/src/python/pants/goal/anonymous_telemetry.py
index d907c54548c..96a8bd744b1 100644
--- a/src/python/pants/goal/anonymous_telemetry.py
+++ b/src/python/pants/goal/anonymous_telemetry.py
@@ -22,15 +22,14 @@
 )
 from pants.engine.unions import UnionRule
 from pants.option.subsystem import Subsystem
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 
 logger = logging.getLogger(__name__)
 
 
 _bugout_access_token = "3ae76900-9a68-4a87-a127-7c9f179d7272"
 _bugout_journal_id = "801e9b3c-6b03-40a7-870f-5b25d326da66"
-_telemetry_docs_url = bracketed_docs_url("anonymous-telemetry")
-_telemetry_docs_referral = f"See {_telemetry_docs_url} for details"
+_telemetry_docs_referral = f"See {doc_url('anonymous-telemetry')} for details"
 
 
 class AnonymousTelemetry(Subsystem):
diff --git a/src/python/pants/init/logging.py b/src/python/pants/init/logging.py
index 9e9114885ed..50788a40ab9 100644
--- a/src/python/pants/init/logging.py
+++ b/src/python/pants/init/logging.py
@@ -15,7 +15,7 @@
 from pants.engine.internals import native_engine
 from pants.option.option_value_container import OptionValueContainer
 from pants.util.dirutil import safe_mkdir_for
-from pants.util.docutil import unbracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.logging import LogLevel
 from pants.util.strutil import strip_prefix
 
@@ -61,8 +61,8 @@ def formatException(self, exc_info):
         )
 
         return (
-            f"{stacktrace}\n\n({debug_instructions}See {unbracketed_docs_url('troubleshooting')} for common issues. "
-            f"Consider reaching out for help: {unbracketed_docs_url('getting-help')}.)"
+            f"{stacktrace}\n\n({debug_instructions}See {doc_url('troubleshooting')} for common issues. "
+            f"Consider reaching out for help: {doc_url('getting-help')}.)"
         )
 
 
diff --git a/src/python/pants/option/global_options.py b/src/python/pants/option/global_options.py
index cec1e47989f..21798b985ba 100644
--- a/src/python/pants/option/global_options.py
+++ b/src/python/pants/option/global_options.py
@@ -32,7 +32,7 @@
 from pants.option.scope import GLOBAL_SCOPE
 from pants.option.subsystem import Subsystem
 from pants.util.dirutil import fast_relpath_optional
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.logging import LogLevel
 from pants.util.ordered_set import OrderedSet
 from pants.util.osutil import CPU_COUNT
@@ -573,7 +573,7 @@ def register_bootstrap_options(cls, register):
             help="Use this Pants version. Note that Pants only uses this to verify that you are "
             "using the requested version, as Pants cannot dynamically change the version it "
             "is using once the program is already running.\n\nIf you use the `./pants` script from "
-            f"{bracketed_docs_url('installation')}, however, changing the value in your "
+            f"{doc_url('installation')}, however, changing the value in your "
             "`pants.toml` will cause the new version to be installed and run automatically.\n\n"
             "Run `./pants --version` to check what is being used.",
         )
@@ -1254,7 +1254,7 @@ def register_options(cls, register):
             metavar="[+-]tag1,tag2,...",
             help=(
                 "Include only targets with these tags (optional '+' prefix) or without these "
-                f"tags ('-' prefix). See {bracketed_docs_url('advanced-target-selection')}."
+                f"tags ('-' prefix). See {doc_url('advanced-target-selection')}."
             ),
         )
         register(
@@ -1314,7 +1314,7 @@ def register_options(cls, register):
             default=[],
             help=(
                 "Python files to evaluate and whose symbols should be exposed to all BUILD files. "
-                f"See {bracketed_docs_url('macros')}."
+                f"See {doc_url('macros')}."
             ),
         )
         register(
diff --git a/src/python/pants/source/source_root.py b/src/python/pants/source/source_root.py
index 55154d916dc..45db67eb498 100644
--- a/src/python/pants/source/source_root.py
+++ b/src/python/pants/source/source_root.py
@@ -17,7 +17,7 @@
 from pants.engine.rules import Get, MultiGet, collect_rules, rule
 from pants.engine.target import Target
 from pants.option.subsystem import Subsystem
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.util.frozendict import FrozenDict
 from pants.util.logging import LogLevel
 from pants.util.memo import memoized_method
@@ -42,9 +42,7 @@ class SourceRootError(Exception):
     """An error related to SourceRoot computation."""
 
     def __init__(self, msg: str):
-        super().__init__(
-            f"{msg}See {bracketed_docs_url('source-roots')} for how to define source roots."
-        )
+        super().__init__(f"{msg}See {doc_url('source-roots')} for how to define source roots.")
 
 
 class InvalidSourceRootPatternError(SourceRootError):
@@ -113,7 +111,7 @@ def register_options(cls, register):
             "`<buildroot>/project1/src/python`. A `*` wildcard will match a single path segment, "
             "e.g., `src/*` will match `<buildroot>/src/python` and `<buildroot>/src/rust`. "
             "Use `/` to signify that the buildroot itself is a source root. "
-            f"See {bracketed_docs_url('source-roots')}",
+            f"See {doc_url('source-roots')}.",
         )
         register(
             "--marker-filenames",
diff --git a/src/python/pants/util/docutil.py b/src/python/pants/util/docutil.py
index b0efa822d73..96f3eaa8502 100644
--- a/src/python/pants/util/docutil.py
+++ b/src/python/pants/util/docutil.py
@@ -1,7 +1,14 @@
 # Copyright 2020 Pants project contributors (see CONTRIBUTORS.md).
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
+from __future__ import annotations
+
+import re
 import shutil
+from html.parser import HTMLParser
+from typing import Iterable, cast
+
+import requests
 
 from pants.version import MAJOR_MINOR
 
@@ -12,23 +19,92 @@ def terminal_width(*, fallback: int = 96, padding: int = 2) -> int:
     return shutil.get_terminal_size(fallback=(fallback, 24)).columns - padding
 
 
-def bracketed_docs_url(slug: str) -> str:
-    """Link to the Pants docs using the current version of Pants.
+def doc_url(slug: str) -> str:
+    return f"https://www.pantsbuild.org/v{MAJOR_MINOR}/docs/{slug}"
 
-    Returned URL is surrounded by parentheses, to prevent linkifiers from considering any
-    adjacent punctuation (such as a period at the end of a sentence) as part of the URL.
 
-    Note that this function used to use square brackets, hence the name, but it turns out
-    that those prevent any linkification at all from happening on readme.com, so we switched
-    to parens, but didn't update the name to prevent churn.
-    """
-    return f"({unbracketed_docs_url(slug)})"
+# Code to replace doc urls with appropriate markdown, for rendering on the docsite.
 
+_doc_url_pattern = r"https://www.pantsbuild.org/v(\d+\.[^/]+)/docs/(?P<slug>[a-zA-Z0-9_-]+)"
 
-def unbracketed_docs_url(slug: str) -> str:
-    """Link to the Pants docs using the current version of Pants.
 
-    Returned URL is _not_ surrounded by parentheses. This should only be used in error messages. Use
-    `bracketed_docs_url` for help messages so that linkifiers work correctly.
-    """
-    return f"https://www.pantsbuild.org/v{MAJOR_MINOR}/docs/{slug}"
+class DocUrlMatcher:
+    """Utilities for regex matching docsite URLs."""
+
+    def __init__(self):
+        self._doc_url_re = re.compile(_doc_url_pattern)
+
+    def slug_for_url(self, url: str) -> str:
+        mo = self._doc_url_re.match(url)
+        if not mo:
+            raise ValueError(f"Not a docsite URL: {url}")
+        return cast(str, mo.group("slug"))
+
+    def find_doc_urls(self, strs: Iterable[str]) -> set[str]:
+        """Find all the docsite urls in the given strings."""
+        return {mo.group(0) for s in strs for mo in self._doc_url_re.finditer(s)}
+
+
+class DocUrlRewriter:
+    def __init__(self, slug_to_title: dict[str, str]):
+        self._doc_url_re = re.compile(_doc_url_pattern)
+        self._slug_to_title = slug_to_title
+
+    def _rewrite_url(self, mo: re.Match) -> str:
+        # The docsite injects the version automatically at markdown rendering time, so we
+        # must not also do so, or it will be doubled, and the resulting links will be broken.
+        slug = mo.group("slug")
+        title = self._slug_to_title.get(slug)
+        if not title:
+            raise ValueError(f"Found empty or no title for {mo.group(0)}")
+        return f"[{title}](doc:{slug})"
+
+    def rewrite(self, s: str) -> str:
+        return self._doc_url_re.sub(self._rewrite_url, s)
+
+
+class TitleFinder(HTMLParser):
+    """Grabs the page title out of a docsite page."""
+
+    def __init__(self):
+        super().__init__()
+        self._in_title: bool = False
+        self._title: str | None = None
+
+    def handle_starttag(self, tag, attrs):
+        if tag == "title":
+            self._in_title = True
+
+    def handle_endtag(self, tag):
+        if tag == "title":
+            self._in_title = False
+
+    def handle_data(self, data):
+        if self._in_title:
+            self._title = data.strip()
+
+    @property
+    def title(self) -> str | None:
+        return self._title
+
+
+def get_title_from_page_content(page_content: str) -> str:
+    title_finder = TitleFinder()
+    title_finder.feed(page_content)
+    return title_finder.title or ""
+
+
+def get_title(url: str) -> str:
+    return get_title_from_page_content(requests.get(url).text)
+
+
+def get_titles(urls: set[str]) -> dict[str, str]:
+    """Return map from slug->title for each given docsite URL."""
+
+    matcher = DocUrlMatcher()
+    # TODO: Parallelize the http requests.
+    #  E.g., by turning generate_docs.py into a plugin goal and using the engine.
+    ret = {}
+    for url in urls:
+        ret[matcher.slug_for_url(url)] = get_title(url)
+    return ret
diff --git a/src/python/pants/util/docutil_test.py b/src/python/pants/util/docutil_test.py
new file mode 100644
index 00000000000..c6b2e819187
--- /dev/null
+++ b/src/python/pants/util/docutil_test.py
@@ -0,0 +1,56 @@
+# Copyright 2021 Pants project contributors (see CONTRIBUTORS.md).
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+import textwrap
+
+import pytest
+
+from pants.util.docutil import DocUrlMatcher, DocUrlRewriter, doc_url, get_title_from_page_content
+
+
+@pytest.mark.parametrize("slug", ["foo-bar", "baz3", "qux"])
+def test_slug_for_url(slug: str) -> None:
+    assert DocUrlMatcher().slug_for_url(doc_url(slug)) == slug
+
+
+def test_slug_for_url_error() -> None:
+    with pytest.raises(ValueError) as excinfo:
+        DocUrlMatcher().slug_for_url("https://notthedocsite.com/v2.6/foobar")
+    assert "Not a docsite URL" in str(excinfo.value)
+
+
+def test_find_doc_urls() -> None:
+    matcher = DocUrlMatcher()
+    strs = [
+        f"See {doc_url('foo-bar')} for details.",
+        f"See {doc_url('qux')}.",  # Don't capture trailing dot.
+        f"See {doc_url('foo-bar')} and {doc_url('baz3')}",  # Multiple urls in string.
+    ]
+    assert matcher.find_doc_urls(strs) == {doc_url(slug) for slug in ["foo-bar", "baz3", "qux"]}
+
+
+def test_get_title_from_page_content():
+    page_content = textwrap.dedent(
+        """
+      <!DOCTYPE html><html ng-app="hub" lang="en" style="" class=" useReactApp  ">
+      <head>
+      <script src="blahblah"></script>
+      <meta charset="utf-8"><meta http-equiv="X-UA-Compatible" content="IE=edge">
+      <title ng-bind="pageTitle">Welcome to Pants!</title>
+      <meta name="description" content="Documentation for the Pants v2 build system.">
+      </head>
+      <body>Welcome to Pants, the ergonomic build system!</body>
+    """
+    )
+    assert get_title_from_page_content(page_content) == "Welcome to Pants!"
+
+
+def test_doc_url_rewriter():
+    dur = DocUrlRewriter(
+        {
+            "foo": "Foo",
+            "bar": "Welcome to Bar!",
+        }
+    )
+    assert dur.rewrite(f"See {doc_url('foo')} for details.") == "See [Foo](doc:foo) for details."
+    assert dur.rewrite(f"Check out {doc_url('bar')}.") == "Check out [Welcome to Bar!](doc:bar)."
diff --git a/src/python/pants/vcs/changed.py b/src/python/pants/vcs/changed.py
index df6bd1309b9..99af4058b83 100644
--- a/src/python/pants/vcs/changed.py
+++ b/src/python/pants/vcs/changed.py
@@ -16,7 +16,7 @@
 from pants.engine.rules import Get, collect_rules, rule
 from pants.option.option_value_container import OptionValueContainer
 from pants.option.subsystem import Subsystem
-from pants.util.docutil import bracketed_docs_url
+from pants.util.docutil import doc_url
 from pants.vcs.git import Git
 
 
@@ -89,8 +89,8 @@ def changed_files(self, git: Git) -> List[str]:
 class Changed(Subsystem):
     options_scope = "changed"
     help = (
-        "Tell Pants to detect what files and targets have changed from Git.\n\nSee "
-        f"{bracketed_docs_url('advanced-target-selection')}."
+        "Tell Pants to detect what files and targets have changed from Git.\n\n"
+        f"See {doc_url('advanced-target-selection')}."
     )
 
     @classmethod
diff --git a/src/rust/engine/src/externs/mod.rs b/src/rust/engine/src/externs/mod.rs
index 5d07be1fe91..f2be13cebf6 100644
--- a/src/rust/engine/src/externs/mod.rs
+++ b/src/rust/engine/src/externs/mod.rs
@@ -256,12 +256,12 @@ pub fn val_to_log_level(obj: &PyObject) -> Result<log::Level, String> {
 }
 
 /// Link to the Pants docs using the current version of Pants.
-pub fn bracketed_docs_url(slug: &str) -> String {
+pub fn doc_url(slug: &str) -> String {
   let gil = Python::acquire_gil();
   let py = gil.python();
   let docutil = py.import("pants.util.docutil").unwrap();
   docutil
-    .call(py, "bracketed_docs_url", (slug,), None)
+    .call(py, "doc_url", (slug,), None)
     .unwrap()
     .extract(py)
     .unwrap()
diff --git a/src/rust/engine/src/nodes.rs b/src/rust/engine/src/nodes.rs
index 4b008211b8d..5f21bbf44af 100644
--- a/src/rust/engine/src/nodes.rs
+++ b/src/rust/engine/src/nodes.rs
@@ -499,7 +499,7 @@ fn unmatched_globs_additional_context() -> Option<String> {
     "\n\nDo the file(s) exist? If so, check if the file(s) are in your `.gitignore` or the global \
     `pants_ignore` option, which may result in Pants not being able to see the file(s) even though \
     they exist on disk. Refer to {}.",
-    externs::bracketed_docs_url("troubleshooting#pants-cannot-find-a-file-in-your-project")
+    externs::doc_url("troubleshooting#pants-cannot-find-a-file-in-your-project")
   ))
 }